Btobdant idyestttfes of the thiazine sebies



Patented Jan. 19, 1932 RICHARD HERZ AND noRBEn'r" STEIGER, or rnnmgroanoit-rnn-mnin, cannery;-

ASSIG-NORS T GENERAL ANILINE worms, 11m, OIILNEW. YOBK,. N,; 1, [A coarlom- TION or DELAWARE nonmmr nynsrurrs or mejs z 'ssmst no Drawing. Application filed October 2, 1929, Serial NoQ 39 6,93O,' and"in Gem-11 octbbef "161 19281 Our present invention relates to new mordant dyestuffs, more particularlylit relates to valuable mordan't dyestuffs which are obtain able by treating VhydroXy suIfoaryliJninO- naphthoquinonesof the general formula i duc ed probably correspond to the general wherein the naphthalene and the aryl nucleus .1 I. ary1S0;H

wherein the naphthalene and the aryl nucleus may contain further substituents, with sulfurizing agents. The dyestuffs thus proformula may contain further substituents. The hydroXy-sulfoaryliniino-naphthoquinones used 'as starting materials. in our process may be prepared by condensing -1 .2-.naphthoquinone or its substitution piodiictsfas sulfonic acids;

with amino-arylsulfonic acids. N

Dyestuffs of this kind are already described in our U. Patent No. 1,497,720. But

according to the processof the said patent;

by which the sulfonic groups are introduced fonic groups. In consequence of this uniformity the dyestuflspossess especially good dyeing'properties. As a greatnumber of amino-aryl-sulfonic acids can be easilyob-.

tained, numerous dyestufis may be produced according toourprocess in a simple'way and powder, soluble in adilute caustic soda solu- 100 in a great purity. Ofaspecial value are those derlved from meta-amino-aryl-sulfonicacids. I

As to their tinctorial behaviour the dye-- stuffs obtained by-our process are acid mor a and indilute acids,- especially in acetic acid. The acid solution"exhibits'.a reddish violet 'tint,turning to blue on the addition of an alkali. The dyestuffs dye the animal 'fiber from the acid bath and yield when'afterdant dyestuffs- They are soluble in: water chromed bright green shades. They may also befemployed for; printing'wool or cottonac cordingto the chrome-printing processes-f "In order to flirtherfillustrate' our invention thefollowing examples are given,,thefparts being by weight and all temperatures in centi grade degrees, but we wishit to be understood that. "we are notlimitedgtliftlijei particular products nor reaction: conditions mentioned .thereink n 117 partsof 2 -hydroXy-4- (r-nieth l-a sulfoephen'yli nino)lsienaphthoquinone(obtain able for instance by condensing."1.2snaphthog quinoneL-4;sulfonic acidl-amino tmeth yl-benzene-2e2 sulfonic;acid).;:are introduced at 209302 into 5 a solution J of .1 12 parts of sulfur in 250 parts of fuming sulfuricacidfof 28%" strength'. f Themassislslowly heated lto 40, stirred at this temperature for about 4 hours and then poured into ice. cipitated dyestufi' is filtered off and washed with common salt probably to the formula: ,7

TOH: I d

The presolutiomiflt corresponds V the a reddish violet tion to a blue solution which becomes bright reddishviolet when acidified. It dyes wool from an acid bath reddish violet shades turning to bright green when afterchromed.

Emmy/2Z6 j 40 parts of 2-hydroxy-d-(3' sulfophenylij rhino) -1'-'.4t-naphthoquinone are introduced at -30 into-a solutionof 8 parts or' sulfur in 400 parts of fuming sulfuric acid of strength.v The mass is treated as described in Example 1. The dyestufi' thus produced corresponds probablywto'the formula 2. 7

soar! .prioducts preparedh forinstance :frorn;1.2v

naphthoquinone, LQ naphth quinoneAksul fonic acidior ll2anaphthoquino ne-i6-disulfonic acid 7 onthe onehand and 1-me'thyl-etaminobenzene-fi-sulfonic acid or an aminonaphthalene sulfonic acid on the other hand. 'We claim:- I V I 11 As new products :the imordant dyestufi's ofrrthei probable general formula:

. 0' e m 7 nwherein aryl represents a, naphthalene nucleus, or. a benzene nucleus whichmay contain methyl groups, and? X means hydrogen or a sulfonic acid group;.which products are violet colored powders,soluble in water and acidified water, with a reddish violet tint which turns to blue on'the addition of an alkali, dyeing woolfroln an acid bath reddish violet shades becoming greenish-when after};

chromed;

. shades becoming 2. As new products the mordant dyestuffs of the probable general formula:

wherein the benzene" nucleus may contain methyl groups. which compounds are violet colored powders, soluble in water and acidified water with areddishiviolet. tint which turns to blue onzthe'additioni of an alkali,.dyeing woolfrom an-acidjbath reddish violet greenish -Whenafter= chromed- 3. As a new productthe mordant dyestufi of the probable formula;

which product is a reddish violet powder;

soluble in a dilute caustic soda solution with a blue coloration which-"becomes bright reddish violet when acidified, dyeing wool from an acid bath reddish, violet shades turning to bright green when afterchromed.

4. As a new product the mordant of the probable formula 2.

dyestuff doan I which productis a violet-powder, very easily 7 soluble inwater with a bright claret-red tint which turns toblue of the addition of an alkali, dyeing woolfrom an acid bathcl'aretrc'dshades becoming bluish green'when afterchromed.

'In testimony whereof; we afi'ix our. signatures. I

RICHARD HERZ;

. .NORBERT STEIGER. 

